Journal Article A short synthesis of (+)-β-lycorane by asymmetric conjugate addition cascade

Nishimura, Katsumi  ,  Fukuyama, Naoshi  ,  Yasuhara, Tomohisa  ,  Yamashita, Mitsuaki  ,  Sumiyoshi, Takaaki  ,  Yamamoto, Yasutomo  ,  Yamada, Ken-ichi  ,  Tomioka, Kiyoshi

Tetrahedron
71 ( 39 )  , pp.7222 - 7226 , 2015-09-30 , Elsevier Ltd.
ISSN:0040-4020
NCID:AA00861787
Description
The chiral diether ligand-controlled asymmetric conjugate addition of organolithiums to nona-2, 7-dienedioate and subsequent intramolecular conjugate addition of the enolate intermediate gave all-trans trisubstituted cyclohexanes with high ee and yields. Using this methodology, an efficient short asymmetric total synthesis of (+)-β-lycorane was accomplished in 33% overall yield through five steps from the dienedioate.
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